DE3705389A1 - SUBSTITUTED CROTON ACID ESTERS AND FUNGICIDES CONTAINING THEM - Google Patents

Abstract

Substituted crotonates of the formula <IMAGE> (I) where R1 is alkyl, R2 is hydrogen, alkyl or alkoxy, X is halogen, cyano, trifluoromethyl, nitro, alkyl, alkoxy, phenyl, phenoxy, benzyloxy or hydrogen, m is from 1 to 5, and Y is methylenoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen, and fungicides containing them.

Description

The present invention relates to new crotonic acid ester derivatives, their Manufacture and its use as fungicides.

It is known to use N-tridecyl-2,6-dimethylmorpholine or its salts, e.g. B. the acetate to be used as fungicides (DE 11 64 152, 11 73 722). Your However, the effect is insufficient in some cases.

It is also known that some substituted acrylic acid ester derivatives have fungicidal properties (EP 1 78 826, DE 35 19 282.8, DE 35 19 280.1).

It has now been found that new crotonic acid ester derivatives of the formula I

in the

R¹C₁-C₅-alkyl, R²hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, X same or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, optionally substituted phenyl, optionally substituted Phenoxy, optionally substituted benzyloxy or hydrogen, m 1 to 5 and Ymethyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen

means, in addition to a very high fungitoxic effect, also a very good one Have plant tolerance.

The new compounds of formula I fall due to their preparation the C = C double bond as E / Z isomer mixtures which, in the usual way, e.g. B. by crystallization or chromatography, in the individual Components can be separated. Both the individual isomers Compounds as well as their mixtures are encompassed by the invention.  

X is preferably hydrogen, 2-fluorine, 3-fluorine, 4-fluorine, 2-chloro-6- fluorine, 2-chloro, 3-chloro, 4-chloro, 2-bromo, 3-bromo, 4-bromo, 2,4-dichloro, 2,6-dichloro-, 3,5-dichloro-, 2,4,6-trichloro, 2-chloro-4-methyl-, 2-methyl-4-chloro, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-isopropyl, 4-tert-butyl, 2,4-dimethyl, 2,6-dimethyl, 2,4,6-trimethyl, 2-methoxy-4-methyl, 4-methoxy-2-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 4-ethoxy, 4-isopropoxy, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-cyano, 3-cyano, 4-cyano, 3-nitro, 4-nitro-, 4-phenyl, 4-benzyloxy-, 4-phenoxy, halophenoxy, 4- (2-chloro) - phenoxy-, 4- (2,4-dichloro) -phenoxy-, C₁-C₄-alkylphenoxy, 4- (2-methyl) - phenoxy, 3-benzyloxy, halogenobenzyloxy, 3- (2-chloro) benzyloxy, 3- (2,4-dichloro) benzyloxy, 3- (2-fluoro) benzyloxy, 3- (4-bromo) benzyloxy, C₁-C₄-alkylbenzyloxy-, 3- (2-methyl) -benzyloxy-, 3-phenoxy-, 3- (2-chloro) - phenoxy-, 3- (2,4-dichloro) -phenoxy-, 3- (2-fluoro) -phenoxy-, 3- (4-bromo) - phenoxy, 3- (2-methyl) -phenoxy-, R² hydrogen, methyl, ethyl, propyl, Butyl, methoxy, ethoxy, isopropoxy, butoxy, R¹ C₁-C₃-alkyl, methyl, ethyl, i-propyl and Y is a -CH₂O-, -OCH₂-, -CH₂-CH₂-, -CH = CH-, -C≡C group or stands for O.

The new compounds can be prepared by using an α- ketocarboxylic acid ester of the formula II,

in which X _m , Y and R¹ have the meanings given above, in a Wittig reaction with an alkyl or alkoxymethyltriphenylphosphonium bromide in the presence of a base such as, for. B. n-butyllithium, sodium methylate, potassium tert-butoxide or sodium hydride (see G. Wittig and U. Schöllkopf, Org. Synth., Coll. Vol. V, 751-54 [1973]).

The α- ketocarboxylic acid esters of the formula II can, for. B. by the reaction of the corresponding aromatic Grignard compounds with imidazolides of the formula III

be prepared (J. S. Nimitz, H. S. Mosher, J. Org. Chem. 1981, 46, 211-213), where R¹ has the meanings given above.  

The preparation of the new compounds of formula I is as follows Example explained.

Manufacturing example a) Preparation of methyl 2- (benzyloxy) phenylglyoxylate

0.1 mol of the Grignard compound prepared from 1-benzyloxy-2-bromobenzene and magnesium shavings in tetrahydrofuran are slowly added dropwise under nitrogen at -50 ° C. to 14.6 g (95 mmol) of methyloxalylimidazole in tetrahydrofuran. The mixture is allowed to slowly come to room temperature (20 ° C.) over a period of 4 hours. It is poured onto ice water and extracted several times with ether. The combined ether phases are washed neutral and dried. After evaporation of the solvent, the product is crystallized with n-pentane. 16 g (62%) of colorless crystals of the above-mentioned compound are obtained.
1 H-NMR (CDCl₃): w = 3.35 (S, 3H), 5.07 (S, 2H), 7.05 (m, 2H), 7.40 (m, 5H), 7.55 (m , 1H), 7.90 (m, 1H).

b) Preparation of methyl 2- [2- (benzyloxy) phenyl] crotonic acid (compound no. 83)

18.5 g (50 mmol) of ethyl triphenylphosphonium bromide are placed in 100 ml of absolute tetrahydrofuran and 32 ml (50 mmol) of a 1.6 molar solution of n-butyllithium in hexane are slowly added at 0 ° C. under nitrogen. After stirring for 30 minutes, 13.5 g (50 mmol) of methyl 2- (benzyloxy) phenylglyoxylate in 25 ml of absolute tetrahydrofuran are added dropwise at 0.degree. The mixture is stirred at room temperature for 16 hours. After concentration, the remaining residue is taken up in dichloromethane and washed several times with water. After drying over Na₂SO₄ the solvent is evaporated. The crude product thus obtained is purified by chromatography (cyclohexane / ethyl acetate = 9/1). 8.0 g (57%) of the crotonic acid methyl ester (trans / cis ratio = 9/1) are obtained as an oil.
1 H-NMR (CDCl₃): δ = 1.75 / 2.12 (2 × d, 3H), 3.57 / 3.64 (2 × s, 3H), 5.10 (S, 2H), 6, 30 / 6.90 (2 x q, 1H), 6.95-7.80 (m, 9H).

With a corresponding modification of the above information, those in the Compounds listed in the following table can be synthesized.

Generally speaking, the new compounds are characterized by a excellent effectiveness against a wide range of phytopathogenic agents Mushrooms, in particular from the class of the Ascomycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can can be used as leaf and soil fungicides.

The fungicidal compounds are particularly interesting for combating a variety of different crops or their seeds, in particular Wheat, rye, barley, oats, rice, corn, cotton, soy, Coffee, sugar cane, fruit and ornamental plants in horticulture, viticulture as well Vegetables - such as cucumbers, beans and squash.

The new compounds are particularly suitable for combating the following Plant diseases:

Erysiphe graminis (powdery mildew) in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants,
Podosphaera leucotricha on apples,
Uncinula necator on vines,
Puccinia species on cereals,
Rhizoctonia solani on cotton,
Ustilago species on cereals and sugar cane,
Venturia inaequalis (scab) on apples,
Septoria nodorum on wheat,
Pyrenophora teres on barley,
Botrytis cinerea (gray mold) on strawberries, vines,
Cercospora arachidicola on peanuts,
Pseudocercosporella herpotrichoides on wheat, barley,
Pyricularia oryzae on rice,
Phytophthora infestans on potatoes and tomatoes,
Alternaria solani on potatoes, tomatoes,
Plasmopara viticola on vines as well
Fusarium and Verticillium species on different plants.

The compounds are applied by treating the plants with the active ingredients sprayed or dusted or the seeds of the plants with the active ingredients treated. It is used before or after infection Plants or seeds through the mushrooms.

The new substances can be converted into the usual formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the Uses; in any case, they should be fine and even Ensure distribution of the active substance. The wording are made in a known manner, e.g. B. by stretching the active ingredient with solvents and / or carriers, optionally under Use of emulsifiers and dispersants, in which case Use of water as a diluent also other organic solvents can be used as auxiliary solvents. As auxiliary substances The following are essentially suitable: solvents such as aromatics (e.g. xylene, toluene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), amines (e.g. Ethanolamine, dimethylformamide) and water; Carriers like natural Stone powder, e.g. B. kaolins, clays, talc, chalk and synthetic Rock meal (e.g. highly disperse silica, silicates); Emulsifier, such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol Ethers, alkyl sulfonates and aryl sulfonates) and dispersants, such as Lignin, sulfite liquor and methyl cellulose.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% active ingredient. The application rates are Depending on the type of effect desired, between 0.05 and 3 kg of active ingredient or more per ha.

Some of the new compounds have very good activity against human pathogenic fungi such as Trichophyton mentagrophytes and Candida albicans.

The agents or the ready-to-use preparations made therefrom, such as solutions, emulsions, suspensions, powders, dusts, pastes or Granules are used in a known manner, for example by Spraying, atomizing, dusting, scattering, pickling or pouring.  

Examples of such preparations are:

• I. 90 parts by weight of compound no. 89 are mixed with 10 parts by weight of N-methyl- α- pyrrolidone, and a solution is obtained which is suitable for use in the form of tiny drops.
• II. 20 parts by weight of compound no. 100 are dissolved in a mixture, that from 80 parts by weight of xylene, 10 parts by weight of the adduct from 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight Divide the adduct and 40 moles of ethylene oxide into 1 mole Castor oil is made up. By pouring out and finely distributing the solution in Water gives an aqueous dispersion.
• III. 20 parts by weight of compound no. 89 are dissolved in a mixture, the from 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide There is 1 mole of castor oil. By pouring and finely distributing the Solution in water gives an aqueous dispersion.
• IV. 20 parts by weight of compound no. 100 are dissolved in a mixture, that from 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. Pouring and finely distributing the solution in water gives one an aqueous dispersion.
• V. 80 parts by weight of compound no. 89 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene- α- sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and ground in a hammer mill. A spray mixture is obtained by finely distributing the mixture in water.
• VI. 3 parts by weight of compound no. 100 with 97 parts by weight of finely divided Kaolin mixed intimately. You get one in this way Dusts containing 3% by weight of the active ingredient.
• VII. 30 parts by weight of compound no. 89 are mixed with 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that is sprayed onto the surface of this silica gel was mixed intimately. A preparation is obtained in this way of the active ingredient with good adhesiveness.  
• VIII. 40 parts by weight of compound no. 100 are mixed with 10 parts of sodium salt a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts Silica gel and 48 parts of water mixed intimately. You get one stable aqueous dispersion. By diluting with water you get an aqueous dispersion.
• IX. 20 parts of compound no. 89 are mixed with 2 parts of the calcium salt Dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts sodium salt of a phenolsulfonic acid-urea-formaldehyde Condensate and 68 parts of a paraffinic mineral oil intimately mixed. A stable oily dispersion is obtained.

The agents according to the invention can also be used together in these forms of use with other active ingredients, such as. B. herbicides, insecticides, Growth regulators and fungicides, or also with fertilizers are mixed and applied. When mixed with fungicides in many cases the fungicidal activity spectrum is enlarged.

The following list of fungicides with which the compounds of the invention can be combined, the possible combinations explain, but not limit.

Fungicides which are combined with the compounds according to the invention can include:

Sulfur,
Dithiocarbamates and their derivatives, such as
Ferridimethyldithiocarbamate,
Zinc dimethyldithiocarbamate,
Zinc ethylene bisdithiocarbamate,
Manganese ethylene bisdithiocarbamate,
Manganese-zinc-ethylenediamine-bis-dithiocarbamate,
Tetramethylthiuram disulfide,
Ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate),
Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate),
Zinc (N, N'-propylene-bis-dithiocarbamate),
N, N'-propylene bis (thiocarbamoyl) disulfide;

Nitroderivatives, such as
Dinitro- (1-methylheptyl) phenylcrotonate,
2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate,
2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate,
5-nitro-isophthalic acid di-isopropyl ester,

heterocyclic structures, such as
2-heptadecyl-2-imidazoline acetate,
2,4-dichloro-6- (o-chloroanilino) -s-triazine,
O, O-diethyl phthalimidophosphonothioate,
5-amino-1- (bis- (dimethylamino) phosphinyl) -3-phenyl-1,2,4-triazole,
2,3-dicyano-1,4-dithioanthraquinone,
2-thio-1,3-dithio- (4,5-b) -quinoxaline,
1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester,
2-methoxycarboxylamino-benzimidazole,
2- (furyl- (2) -benzimidazole,
2- (thiazolyl) - (4) -benzimidazole,
N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide,
N-trichloromethylthio-tetrahydrophthalimide,
N-trichloromethylthio-phthalimide;

N-dichlorofluoromethylthio-N ′, N′-dimethyl-N-phenyl-sulfuric acid diamide,
5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole,
2-rhodanmethylthiobenzthiazole,
1,4-dichloro-2,5-dimethoxybenzene,
4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone,
Pyridine-2-thio-1-oxide,
8-hydroxyquinoline or its copper salt,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,
2-methyl-5,6-dihydro-4-H-pyran-3-carboxylic acid anilide,
2-methyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid anilide,
2,4,5-trimethyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide,
N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide,
2-methylbenzoic acid anilide,
2-iodo-benzoic acid anilide,
N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,
Piperazin-1,4-diylbis- (1- (2,2,2-trichloro-ethyl) -formamide,
1- (3,4-dichloroanilino) -1-formylamino-2,2,2-trichloroethane,
2,6-dimethyl-N-tridecyl-morpholine or its salts,
2,6-dimethyl-N-cyclododecyl-morpholine or its salts,
N- [3- (p-tert-butylphenyl) -2-methylpropyl] cis-2,6-dimethylmorpholine,
N- [3- (p-tert-butylphenyl) -2-methylpropyl] piperidine,
1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-t-riazole,
1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole,
N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl-urea,
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, -
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, -
1- (4-phenylphenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol-,
α - (2-chlorophenyl) - α - (4-chlorophenyl) -5-pyrimidine-methanol,
5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine,
Bis (p-chlorophenyl) pyridine methanol,
1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene,
1,2-bis (3-methoxycarbonyl) -2-thioureido) benzene and

various fungicides, such as
Dodecylguanidine acetate,
3- (3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl) glutarimide,
Hexachlorobenzene,
DL-methyl-N- (2,6-dimethyl-phenyl) -N-furoyl (2) -alaninate,
DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester,
N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone,
DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester,
5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine,
3- (3,5-dichlorophenyl) 5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dio-n,
3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin,
N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboxamide, -
2-cyano-N- (ethylaminocarbonyl) -2-methoximino) acetamide,
1- (2- (2,4-dichlorophenyl) pentyl) -1H-1,2,4-triazole,
2,4′-difluoro- α - (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol,
N- (3-chloro-2,6-dinitro-4-trifluoromethylphenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine,
1 - ((bis- (4-Fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole.

For the following experiments, the known active ingredient was used as a comparison N-tridecyl-2,6-dimethylmorpholine (A) and its acetate (B) are used.

Application example 1 Efficacy against powdery mildew

Leaves of "Early Gold" wheat seedlings grown in pots were with aqueous spray liquor, the 80% active ingredient and 20% emulsifier contained in the dry matter, sprayed and 24 hours after Dry the spray coating with oidia (spores) of the powdery mildew (Erysiphe graminis var. Tritici) pollinated. The test plants were then in the greenhouse at temperatures between 20 and 22 ° C and 75 up to 80% relative humidity. After 7 days it was Extent of mildew development determined.  

The result of the test shows that active ingredients Nos. 89 and 100 at application as a 0.025 and 0.006% (wt .-%) spray mixture a better fungicidal activity (90%) than the known active ingredients A and B (70%).

Example of use 2 Efficacy against Plasmopara viticola

Leaves of pot vines of the "Müller-Thurgau" variety were watery Spray liquor, the 80% active ingredient and 20% emulsifier in the dry matter contained, sprayed. To the duration of action of the active ingredients to be able to assess, the plants were dried after the Spray coating set up in the greenhouse for 8 days. Only then were the Leaves with a zoospore suspension of Plasmopara viticola (Vine peronospora) infected. After that, the vines were first used for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse with temperatures between 20 and set up at 30 ° C. After this time the plants became Acceleration of the sporangia carrier outbreak again for 16 hours in the humid chamber. Then the assessment of the Extent of fungal outbreak on the undersides of the leaves.

The result of the test shows that active ingredients Nos. 89 and 100 at good fungicidal activity (90%) when used as a 0.05% spray liquor to have.

Claims (7)

1. Substituted crotonic acid esters of formula I. in the R¹C₁-C₅-alkyl, R²hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, X same or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzyloxy or hydrogen, m is 1 to 5 and Ymethyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen. 2. Compounds of formula I according to claim 1, in which X is hydrogen, 2-fluorine, 3-fluorine, 4-fluorine, 2-chloro-6-fluorine, 2-chlorine, 3-chlorine, 4-chloro, 2-bromo, 3-bromo, 4-bromo, 2,4-dichloro, 2,6-dichloro, 3,5-dichloro-, 2,4,6-trichloro, 2-chloro-4-methyl, 2-methyl-4-chloro, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-isopropyl, 4-tert.- Butyl, 2,4-dimethyl, 2,6-dimethyl, 2,4,6-trimethyl, 2-methoxy-4- methyl, 4-methoxy-2-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 4-ethoxy, 4-isopropoxy, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-cyano, 3-cyano, 4-cyano, 3-nitro, 4-nitro, 4-phenyl, 4-benzyloxy, 4-phenoxy, halophenoxy, 4- (2-chloro) - phenoxy-, 4- (2,4-dichloro) -phenoxy-, C₁-C₄-alkylphenoxy, 4- (2-methyl) - phenoxy, 3-benzyloxy, halogenobenzyloxy, 3- (2-chloro) benzyloxy, 3- (2,4-dichloro) benzyloxy, 3- (2-fluoro) benzyloxy, 3- (4-bromo) - benzyloxy-, C₁-C₄-alkylbenzyloxy-, 3- (2-methyl) -benzyloxy-, 3-phenoxy-, 3- (2-chloro) phenoxy-, 3- (2,4-dichloro) phenoxy-, 3- (2- Fluoro) phenoxy, 3- (4-bromo) phenoxy, 3- (2-methyl) phenoxy, R² Hydrogen, methyl, ethyl, propyl, butyl, methoxy, ethoxy, isopropoxy, butoxy, R¹ C₁-C₃-alkyl, methyl, ethyl, i-propyl and Y a -CH₂O-, -OCH₂-, -CH₂-CH₂-, -CH = CH-, -C≡C group or O means.   3. Fungicidal compositions comprising a compound of the formula I. in the R¹C₁-C₅-alkyl, R²hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, X same or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzyloxy or hydrogen, m is 1 to 5 and Ymethyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen, and an inert carrier. 4. A method for combating fungi, characterized in that a compound of formula I. in the R¹C₁-C₅-alkyl, R²hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, X same or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzyloxy or hydrogen, m 1 to 5 and Ymethyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen, which can act on them or on areas, plants or seeds threatened by fungal attack. 5. A process for the preparation of a fungicidal agent, thereby characterized in that one or more compounds of the formula I according to claim 1 with a solid or liquid carrier and optionally with one or more surfactants mixes. 6. A compound of formula I according to claim 1, characterized in that R¹ is methyl, X 3-chlorine, Y CH₂O and R² H. 7. A compound of formula I according to claim 1, characterized in that R¹ is methyl, X 2-methyl, Y is CH₂O and R² H.